Enterprises may require individuals to plan and/or purchase goods and/or services that they are subsequently reimbursed for. In one example, individuals may need to travel, and pay for expenses during the travel. For example, travel expenses can be paid on an individual basis, where individuals pay for flights, hotels, and/or other travel accommodations based on their needs. In such examples, an absence of contextual information can limit insight into the appropriateness of expenses for a particular individual and/or a particular trip, and/or whether such expenses were necessary. Further, it can be a relatively burdensome, manual effort to differentiate between necessary/unnecessary expenses. For example, the travel expenses are subsequently scrutinized for conformance to enterprise policies, and/or regulatory schema. Non-conforming travel expenses can be resource-burdensome to audit.